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Cyclic ester dual cure resins for additive manufacturing

a technology of additive manufacturing and cyclic ester, which is applied in the direction of manufacturing tools, prosthesis, other domestic objects, etc., can solve the problems of general limitation of the material used in such apparatuses

Active Publication Date: 2019-12-10
CARBON INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent is about adding certain chemicals to a liquid or resin to speed up the creation of objects in a three-dimensional printing process. A Lewis acid or an oxidizable tin salt can be added in small amounts to accelerate the formation of the intermediate object.

Problems solved by technology

Materials for use in such apparatus are generally limited, and there is a need for new resins to provide diverse material properties for different product families if three-dimensional fabrication is to achieve its full potential.

Method used

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  • Cyclic ester dual cure resins for additive manufacturing
  • Cyclic ester dual cure resins for additive manufacturing
  • Cyclic ester dual cure resins for additive manufacturing

Examples

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Effect test

examples 1-4

[0116]Conventionally, UV curable bioabsorbable materials are based on di-methacrylate / acrylate terminated crosslinkers with bioabsorbable oligomers as the linkage. Such linkage may be polyethylene glycol (PEG), polylactic acid (PLA), polyglycolic acid (PGA), polycaprolactone (PCL), polydioxanone (PDO), poly(4-hydroxybutyrate) (P4HB), and their copolymers. Although this approach works in producing UV curable bioabsorbable materials, the resulting material can have a high fraction of methacrylate / acrylate backbone which is generally considered non-bioabsorbable. Upon complete degradation of the bioabsorbable linkages, carboxylic acid groups are produced on methacrylate / acrylate backbone, making it soluble in aqueous environment. However, if the molecular weight of methacrylic / acrylic acid is higher than 30,000, the backbone becomes difficult to dissolve in an aqueous environment.

[0117]An orthogonal curing system can potentially mitigate these issues. In addition to the UV curable netw...

example 1

[0120]

[0121]An alcohol is used as the initiator. The ring-opening polymerization is catalyzed by Tin(II) Octoate at elevated temperatures (>60° C.). The reason for curing above 60° C. is that polycaprolactone is crystalline and melts slightly below 60° C. To obtain a significant polymerization rate, the product must be in liquid state.

example 2

[0122]

[0123]An alcohol is used as the initiator. The ring-opening polymerization is catalyzed by a basic organocatalyst, commonly 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), N-methyl-TBD (MTBD), and 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU). TBD was shown to be most effective in catalyzing ring-opening polymerization of caprolactone. See Lohmeijer et al., “Guanidine and Amidine Organocatalysts for Ring-opening Polymerization of Cyclic Esters,”Macromolecules 2006, 39, 8574-8583.

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Abstract

Disclosed herein are methods of forming a three-dimensional object having a biodegradable or bioerodible polymer or copolymer. In some embodiments, the methods include providing a dual cure resin with a photoinitiator, monomers and / or prepolymers that are polymerizable by exposure to actinic radiation or light, at least one cyclic ester, a ring-opening polymerization initiator, and a ring-opening polymerization catalyst. Resins useful for carrying out such methods, and products produced from such methods, are also described.

Description

RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Patent Application Ser. No. 62 / 270,646, filed Dec. 22, 2015, the disclosures of which are incorporated by reference herein in their entirety.FIELD OF THE INVENTION[0002]The present invention concerns materials, methods and apparatus for the fabrication of solid three-dimensional objects from liquid materials, and objects so produced.BACKGROUND OF THE INVENTION[0003]In conventional additive or three-dimensional fabrication techniques, construction of a three-dimensional object is performed in a step-wise or layer-by-layer manner. In particular, layer formation is performed through solidification of photo curable resin under the action of visible or UV light irradiation. Two techniques are known: one in which new layers are formed at the top surface of the growing object; the other in which new layers are formed at the bottom surface of the growing object. An early example is Hull, U.S. Pat. No. 5,236,63...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08F2/46B29C64/129C08G63/78A61K9/00A61L27/54A61L27/58A61L31/16A61L31/14B33Y70/00B33Y80/00B33Y10/00C08G63/08C08F2/50C08G61/04B29C35/08B29K33/04B29L31/00
CPCB29C64/129A61L27/54A61L31/148A61L31/16B33Y80/00A61K9/0051B33Y10/00C08G63/78A61L27/58C08G63/08A61K9/0021B33Y70/00B29C2035/0833B29K2033/04B29C2035/0855A61L2430/02B29K2995/006B29L2031/7532B29C71/02B29C71/0009B29C64/124B29C71/04A61K9/0024B29C35/0805B29C2071/0045B33Y70/10
Inventor GU, XINYUROLLAND, JASON P.
Owner CARBON INC
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